Hydration of Acetylene: A 125th AnniversaryDmitry A. Ponomarev and Sergey M. ShevchenkoThe discovery the hydration of alkynes catalyzed by mercury ions by Mikhail Kucherov made possible industrial production of acetaldehyde from acetylene and had a profound effect on the development of industrial chemistry in the 1920th centuries.Ponomarev, Dmitry A.; Shevchenko, Sergey M. J. Chem. Educ.2007, 84, 1725.

Addition Reactions |

Aldehydes / Ketones |

Alkynes |

Catalysis |

Industrial Chemistry |

Reactions

A Research-Based Laboratory Course in Organic ChemistryThomas A. Newton, Henry J. Tracy, and Caryn PrudentéDescribes the development, implementation, evolution, and evaluation of a unique approach to laboratory instruction in organic chemistry. The new course involves a combinatorial strategy that offers every student a different group of 14 metallole as their personal synthetic target. Newton, Thomas A.; Tracy, Henry J.; Prudenté, Caryn. J. Chem. Educ.2006, 83, 1844.

Combinatorial Chemistry |

Organometallics |

Synthesis |

Undergraduate Research

Stereospecific Synthesis of the Geometrical Isomers of a Natural ProductT. Grove, D. DiLella, and E. VolkerPresents an experiment for the synthesis of (Z) and (E) isomers that is presented to students as a puzzle in which they must determine the identity of the major component in anise oil. A necessary part of the analysis is the preparation the (E) and (Z) isomers of anethole. Molecular modeling is used to explore the conformation of and energy difference between isomers.Grove, T.; DiLella, D.; Volker, E. J. Chem. Educ.2006, 83, 1055.

Ozonolysis Problems That Promote Student ReasoningRay A. Gross Jr.The structural features inherent in acyclic monoterpenes that follow the isoprene rule often lead to unique sets of ozonolysis products from which their structures, excluding stereochemistry, can be determined from molecular formulas only. This article shows how students may elucidate the structures of these compounds by analysis of the oxidative and reductive workup products.Gross, Ray A., Jr. J. Chem. Educ.2006, 83, 604.

Just Click It: Undergraduate Procedures for the Copper(I)-Catalyzed Formation of 1,2,3-Triazoles from Azides and Terminal AcetylenesWilliam D. Sharpless, Peng Wu, Trond Vidar Hansen, and James G. LindbergIn keeping with the defining aspects of click chemistry, this reaction is high-yielding, requires no chromatography, is easily monitored by TLC, and displays distinct peaks in both IR and 1H-NMR. Virtually all products precipitate, and with just a few different starting blocks, every student, or pair of lab partners, can produce a unique "clicked" compound.Sharpless, William D.; Wu, Peng; Hansen, Trond Vidar; Lindberg, James G. J. Chem. Educ.2005, 82, 1833.

Catalysis |

Heterocycles |

Alkynes |

IR Spectroscopy |

NMR Spectroscopy |

Reactions |

Thin Layer Chromatography |

Synthesis

Polypyrazolylborates: ScorpionatesSwiatoslaw TrofimenkoKey features of polypyrazolylborates (also known as scorpionates because of certain specific features of their coordination chemistry) and examples of their use in modeling biologically active compounds are briefly presented.Trofimenko, Swiatoslaw. J. Chem. Educ.2005, 82, 1715.

Coordination Compounds |

Heterocycles |

Synthesis |

Bioinorganic Chemistry |

Molecular Properties / Structure

Organic Functional Group Playing Card DeckMichael J. WelshOrganic functional group playing card deck used for review of the name and structure of organic functional groups that can be used to play any game that a normal deck of cards is used for.Welsh, Michael J. J. Chem. Educ.2003, 80, 426.

The Electrophilic Addition to Alkynes RevisitedThomas T. TidwellA recent claim that vinyl cations are not the predominant intermediates in the electrophilic addition to alkynes is disputed.Tidwell, Thomas T. J. Chem. Educ.1996, 73, 1081.

Addition Reactions |

Alkynes |

Mechanisms of Reactions

A Simple and Safe Catalytic Hydrogenation of 4-Vinylbenzoic AcidDe, Shantanu; Gambhir, Geetu; Krishnamurty, H. G.An alternative procedure to catalytic hydrogenation is catalytic transfer hydrogenation. In this technique, the reduction of an organic compound is achieved with the aid of a donor substance in the presence of a catalyst.De, Shantanu; Gambhir, Geetu; Krishnamurty, H. G. J. Chem. Educ.1994, 71, 992.

A source of isomer-drawing assignmentsKjonaas, Richard A.A comprehensive source from which instructors can choose a wide variety of good isomer drawing examples to use as homework assignments and exam questions.Kjonaas, Richard A. J. Chem. Educ.1992, 69, 452.

A short set of 13C-NMR correlation tablesBrown, D. W.The object of these tables is to enable a student to calculate rapidly approximate d values for 13C nuclei in as wide a variety of compounds as possible.Brown, D. W. J. Chem. Educ.1985, 62, 209.